For making an A5 booklet, google that. There quite a few tutorials.

As for the format...yikes, you have a problem. First off, do you have all the text AS PLAIN TEXT from the various sources? If you do not you have a huge problem, as Word has no way to get it, at least in any automatic way. Word can not talk to those apps. Which means YOU have to get all that text, and YOU have to organize it in the order you want, and YOU have to tell Word that this text (from Facebook say) is this color. That is if you wish to separate Facebook text from other app text.

If you wish to separate chunks by time (as you seem to), then YOU have to determine that, and insert it appropriately.

There could be ways to make thing easier. One would certainly be to use Styles to define things. Like your side could be one Style, her side another.